Tetrahydrofuran → S-(1-acetylazetidin-3-yl) ethanethioate
Reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].[N:5]12[CH2:8][CH:7]1[CH2:6]2.[O:9]1CC[CH2:11][CH2:10]1>>[C:10]([N:5]1[CH2:6][CH:7]([S:3][C:1](=[O:4])[CH3:2])[CH2:8]1)(=[O:9])[CH3:11]Participants
Procedure
With use of 2.00 g of 2-bromomethylaziridine hydrobromide (2) obtained in the above Example 1, there was produced a solution of 1-azabicyclo[1.1.0]butane (4) dissolved in tetrahydrofuran by the same method as in the above Example 7. Next, to a 5 ml solution of dried tetrahydrofuran containing 1.32 ml of thioacetic acid, there was added dropwise a solution of compound (4) dissolved in tetrahydrofuran at a temperature of -40° C. or lower, and the resulting mixture was stirred at a room temperature for 18 hours. After the reaction was over, the solvent was distilled off, and the residue was separated and purified by silica gel column chromatography (eluent: chloroform-acetone), and, thus, there was obtained 828 mg (yield: 51.8%) of 1-acetyl-3-acetylthioazetidine (11).
Workup
- distillationwas distilled off
- customthe residue was separated
- custompurified by silica gel column chromatography (eluent: chloroform-acetone)
Sources & evidence
- ORD record
- ord-248b83d8b7ea4ef8ad1b4533e7dcdf6f
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05659043
Reaction notes
Loading…